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Matthew Bay, Travel Agent in Burlington, KY

Matthew Bay

Burlington, KY Travel Agent

Matthew Bay

Burlington, KY

Wayward Traveling Co, an independent agent with WorldVia, a Travel Leaders Agency
5.0
(3)
100% Recommended
Matt and Amber made our cruise experience absolutely seamless. From helping us pick the perfect itinerary and ship to walking us through stateroom options, port excursions,... Read More >
About
Reviews
Certificates & Awards
My Places
Client Testimonials

Areas of expertise

Destinations:

Walt Disney World, Mexico, Caribbean, Universal Orlando, Disneyland

Interests:

Theme Parks, All Inclusive, Cruises, Family Vacations, Military

Suppliers:

Disney, Royal Caribbean, Universal Parks & Resorts Vacations, Sandals and Beaches Resorts, Inclusive Collection – World of Hyatt

About Me

Love + travel = Wayward Traveling Co.
Love + travel = Wayward Traveling Co.

Hi, I’m Matt, and alongside my wife Amber, we’re the husband-and-wife duo behind Wayward Traveling Co. We’re proud Disney Vacation Experts — and parents of twin newborns — which means we know exactly what it takes to create a magical Disney vacation that works in the real world.

Our clients are families, groups, and couples who want to experience Disney without the overwhelm. We’ve helped parents navigate stroller naps and Lightning Lane strategies, planned unforgettable park days for multi-generational trips, and built itineraries that strike the perfect balance between fun, rest, and making memories.

We believe vacations should be more than a checklist — they should be a story you’ll tell for years. Whether it’s watching your child’s face light up in front of Cinderella Castle, sailing past tropical islands on a cruise, or enjoying a sunset cocktail at a Caribbean all-inclusive, we’re here to make those moments happen.

What We Specialize In

While Disney is our specialty, we also plan:

  • Cruises to the Caribbean
  • Bahamas, Alaska, and beyond
  • All-inclusive resorts in Mexico and the Caribbean
  • Universal Orlando Resort vacations
  • Group getaways for families, friends, and special celebrations

Why Work With Us

  • Real-world experience – We’ve been in the parks with toddlers, navigated crowded holiday weeks, and coordinated large group trips. We’ve stayed in multiple resorts across Disney and the Caribbean, so we give honest, first-hand recommendations.
  • Concierge-level planning – We take care of every detail, from park tickets and dining reservations to excursions, transportation, and special events.
  • Stress-free booking – Most of our vacations come with zero planning fees, so you can enjoy professional travel planning without extra cost.
  • Personal connection – We listen to your needs, customize your trip, and stay in touch before, during, and after your vacation to ensure everything goes smoothly.

A Few Fun Facts About Us

  • We’re annual passholders — We visit Disney multiple times a year to keep up with the latest park updates, events, and hidden gems for our clients.
  • We’ve traveled as a couple, as a group, and now as a family — We understand how different trip styles require different planning approaches.
  • We met through our love of travel — Our first big trip together sealed the deal, and we’ve been exploring the world side-by-side ever since.
  • We’ve been “in your shoes” — From navigating airport security with toddlers to handling last-minute weather changes on cruises, we’ve learned the tricks that keep a trip magical no matter what comes your way.

If you’re dreaming of your next Disney adventure — or a cruise, all-inclusive, or group trip anywhere in the world — we’d love to make it happen for you. Let’s turn your travel plans into memories you’ll treasure forever.

Testimonials

Matt has been just about everywhere and always makes travel easy. I’m coming home from deployment soon and wouldn’t trust anyone else with my vacation plans — plus, he’s definitely Veteran-friendly. – Keenan Wright

He knew so much about every destination we asked about and helped us narrow down the perfect place. Planning felt overwhelming until we talked to Matt — he made everything less stressful. – Jessica Leport

Matt’s planned multiple trips for me, and his attention to detail is unmatched. Every part of the trip is always thoughtful and tailored. He never disappoints! – Angie Huser

REVIEWS

Rating: 5.0
3 reviews
100% Recommended
Your trust is our priority. Every review is submitted by verified travelers after they have booked and completed their trips. Learn more about our review guidelines.
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Showing 3 reviews

Our Dream Cruise—Perfectly Planned!
Reviewed By Cruisewithconfiedence - Louisville, KY | Traveled to Caribbean
Matt and Amber made our cruise experience absolutely seamless. From helping us pick the perfect itinerary and ship to walking us through stateroom options, port excursions, and even what to pack—they thought of everything. We felt so prepared and could truly relax and enjoy every moment. It was our first cruise, and we were a little nervous, but they made us feel confident and excited the whole way through. Their personal recommendations made a huge difference, and we’re already looking at booking our next sailing with them!
Matthew Bay responded
"You just made our day! We’re so happy you had an amazing first cruise and that we could help take the pressure off. Helping you feel confident and excited is exactly why we do what we do. Can’t wait to help you plan the next one—bring on the next adventure! ??"
I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO
Stress-Free Disney Planning from Start to Finish!
Reviewed By DisneyFamily - Cincinnati OH | Traveled to Walt Disney World | Florida | USA
Planning a Disney vacation can be overwhelming, but Matt and Amber made it so easy—and actually enjoyable! They walked us through every step, from choosing the best resort for our family to helping us understand Genie+, dining reservations, and even park hopping. Their tips saved us time, money, and a lot of stress. We saw and did more than we ever thought possible, and our kids are still talking about the trip! If you want to experience the magic of Disney without the planning headaches, book with Matt and Amber. Truly a 5-star experience!
Matthew Bay responded
"Thank you so much for the kind words! We loved helping you plan such a special trip and are so glad everything came together perfectly. It means the world to us that you felt cared for every step of the way. We can’t wait to help you plan the next adventure—wherever it may take you!"
I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO
The best trip of our lives!
Reviewed By HappyTravelers23 - Lexington, KY | Traveled to Ocho Rios | Jamaica | Caribbean
From the very beginning, Matt and Amber made the entire planning process smooth and stress-free. They really took the time to understand what we were looking for and recommended options we never would’ve found on our own. Every detail—from flights and resort bookings to excursions—was perfectly thought out and organized. We felt taken care of the whole way through, and it was clear how much pride they take in making sure their clients have the best experience possible. We can’t wait to book our next adventure with them!
Matthew Bay responded
"Wow—thank you so much! It means the world to us that you felt taken care of every step of the way. We’re so glad everything came together and that you had such an amazing trip. Can’t wait to help you plan the next one—let’s make it even better! ????"
I would recommend this agent to my family and friends.
1 of 1 people found this review helpful. Was this review helpful to you?YES|NO

Certifications & Awards

Celebrity Learning Certification
Celebrity Learning Certification
AMResorts Master Agent
AMResorts Master Agent
Princess Commodore Certified
Princess Commodore Certified
Royal Caribbean University - Bachelor of Adventure
Royal Caribbean University - Bachelor of Adventure
Royal Caribbean University - Master of Adventure
Royal Caribbean University - Master of Adventure

My Places

When it comes to travel planning, real-world experience makes a huge difference. Check out the map below to see all the places I have personally visited or booked for my clients. I know these destinations well and can give you reliable guidance.

Client Testimonials

Disney First Timers
Amber & Matt made our first Disney trip stress-free! They handled every detail from park tickets to dining, so we could just enjoy the magic.
Sarah Whitman – Columbus, OH
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